s0m3thingc1ever, Author at NSFW story — Page 4 of 9

I had sex with one of my best friends after nearly 10 years [MF]

I decided to go visit some friends in New York City just after Christmas one year. It was going to be a whirlwind tour staying with a different person for a night for five nights. Some of these people I knew through family, or from high school, and two of them I had met years before on HotOrNot — which was kind of an early version of Tinder.

All of the friends I was hanging out with were platonic friends. Sure, one of the girls from high school had a crush on me — but it wasn’t reciprocated — and the two girl from HotOrNot had been genuinely good friends to me for so long that I wasn’t trying to push my luck into a hookup. I just liked hanging out with them even if they were both beautiful.

Well, technically, I did sort of try to hook up with each of them once several years prior but I blew it both times. The first I just didn’t make a move on at all. She came to my town, got a hotel, we went out and had a great time, but when it came time to being the man… I just didn’t do it. Thanked her for the great evening and drove home at 2 am leaving both of us unfulfilled. I got into a car accident that night too… I was so distracted thinking about how I fucked up that I hit a parking column. Read more »

Reconnecting and Disconnecting [MF]

I hadn’t seen in her in several years — she had moved away for college and just didn’t make the time to see me if/when she came home. We talked occasionally via call, text, chat, or e-mail and that was what kept me stringing along behind her. It would be fair to say that I was ‘waiting’ for her but only in the emotional sense; I was fucking damn near everyone I could.

Well the time came when she had graduated, come back from traveling overseas, and was down to meet up finally. I was eager as hell and ready to see where things went despite that I knew it was an all-or-nothing decision that was about to be made. I ended things with my FWB, Penny, and everyone else I was dating. Got rid of my hook-up profiles. I was really trying to set the stage for myself to see what happened. Well, here is the synopsis of what happened. Read more »

The webcam was set up and we both came multiple times [MF]

Penny, my long-term friend with benefits, and I had been drifting apart. I had been dating someone semi-seriously for a few months and had not been making time to see Penny. Of course that changed once I broke up with the other woman and I got lonely and horny again. We had a few good reconnecting hook-ups which were almost like post-fight or break-up fucks. Lots of complicated emotions intertwined with a little bit of hate fucking. It was pretty good, honestly.

Once we were more or less ‘back to normal’ we started to settle into our old familiar patterns. Trying to meet couples, sending naughty photos to each other, etc. One morning I woke up incredibly horny and my eyes focused on my computer and the webcam I had set-up directly across from the foot of my bed. An idea flitted through my mind and I decided it would be very fun to film Penny and I fucking again. We had done it once before and enjoyed it. She had wanted to avoid doing it again until she had gotten into better shape. Well the several months I had been with the other woman Penny had been busting her ass, not drinking as much, working out constantly, and was in the best shape of her life post high-school. Read more »

Almost a couple swap… sadly nothing came of it [MF]

***This story doesn’t end in sex, but it came very, very close.***

My FWB, Penny, and I had been trying to meet another couple for a few months. It was surprisingly difficult to find people we considered attractive and who were interested in the type of full-swap situation we were. One day, however, we connected with a couple that lived about an hour north of us in the boondocks.

The wife was gorgeous. Probably Latina or Native American mixed with something. Large breasts, great smile, killer curvy body. The husband looked athletic, jacked, bald-headed and bearded. We talked a few times on AdultFriendFinder, switched to emails between us as couples, and eventually all four of us talked on the phone a few times. We shared nude photos with each other and regular photos of us in our normal lives and the connection seemed really strong.

The other couple were brand new to this and had never tried anything before. Penny and I had done a few things with a few other people, but never a couple so we were the experienced onces in the situation. The wife and I hit it off great and started to text, sext, flirt, and talk on the phone all the time. Penny and the husband not as much, but there was still some effort there. Read more »

The Opera Singer [MF]

My friend with benefits, Penny, and I had been having a complicated on-again-off-again relationship for about three years at this point. I loved her like a friend, the sex was usually incredible, and she was fun to spend time with. However, I didn’t see myself ever wanting to marry her or have kids with her or anything of the sort. I was hitting a point in my life where I was starting to think that it might be the right thing to try to ‘settle down’ and find someone I actually wanted to be with.

I changed my OkCupid profile to one that was looking for something a little more serious and started to message women that I might be interested in. Worth mentioning, Penny and I were also on AdultFriendFinder with a couples profile — though that had stalled out significantly — and I had my own solo profile for trying to find women for something casual. Read more »

I met a couple on Craigslist and fucked her while he watched [MFM]

I found myself scrolling through the Craigslist Personals section one Friday or Saturday night when that still existed. My FWB was on a date with someone — I think — and I was feeling a little lonely and horny. There was post which advertised a meetup with a 26 year old woman and her boyfriend of undefined age. I had been party to a MFM threeway once before a few years ago and had enjoyed the experience. I was open to the idea of trying again and reached out.

I got a reply back pretty quickly with some attached photos. She was gorgeous; a truly stunning woman. Latina; dark hair, eyes, and skin; petite but busty with some beautiful natural curves. She wanted to see a few photos of me in return and I jumped at the bait and sent her a few face pics. I got some praise and a few nudes in return along with the request for a few of my nudes. I sent them way too eagerly, but that worked out well. She and her man were on the hunt and fast replies were what they wanted. Read more »

My roommate confronted me about their foot fetish [M]

I had two roommates, Kurt and Bob. Kurt was a good guy but incredibly socially awkward and a little standoffish. Bob was the exact opposite of Kurt and was incredibly outgoing and people gravitated toward him easily due to his affable nature and jovial personality. Kurt and I had been friends for years and years and I had met Bob through him and we became fast friends — so much so that we ended up living in this apartment for a year. Kurt had a regular 9 – 5 job, so did I, but Bob was an actor and took crazy shifts at crazy times whenever he could. He was always broke but he was always happy about it and as long as he paid the rent and utilities on time I didn’t care what he did.

One afternoon I came home from work early for whatever reason and Bob was home — as always — in the living room, watching cartoons. I kicked off my shoes and jumped on the couch to join him and catch up a bit. We talked a little while and laughed at the nonsense on TV until the program ended. Bob put the TV on mute and asked me if we could talk. Read more »

We argued, we made up, she pissed in my face [MF]

My FWB, Penny, and I had been in a lull for a bit. I think we were both getting bored of each other and, without a ‘love’ connection, there was not a lot of reason to hang out. We would still have sex on a regular basis — but where it has once been 3 or 4 times a night, every single night — it was now 1 or 2 times a night three times a week. The change was probably complicated by my work and living situation and the fact that she had returned back to school to pursue a new career. We had conflicting schedules, I had moved 20 minutes farther away, and being ‘the boss’ at work was killing me with stress.

I tried to break it off with her one night and she wasn’t having it. She drove to my place and a “Say Anything” like stand off took place where she lay on the hood of my car and called me non-stop until I agreed to talk to her. I wanted her off the hood of my car, so I let her in and we locked ourselves in my room while I hoped that my roommates wouldn’t hear our awkward argument. Read more »

She showed up wearing a catholic school girls outfit… because she was a catholic school girl [MF]

The last person I hooked up with on AdultFriendFinder — though not the last person I met or talked to — was a mistake. In fairness, as I have been typing up these stories many of them were mistakes and a wiser me would not have done the things I did. That said, this story deserves it’s rightful place among the others.

I was on the couples profile that I had with my active friend with benefits. Our intent was to find couples to swing or swap with, but I know she talked to a few single guys once in a while and I talked to a few single girls. Neither of us were opposed to inviting a single person to join us, but we were really picky about the guys and unicorns are rarely found in the wild.

One afternoon I was home — I had taken a sick day / mental health day — and was horny and looking for fun. There was a profile of an 18 year old girl that was relatively new, had a few blurry pics, and a little bit of information. I reached out to say hello and got a prompt reply. They were eager to talk to me, liked my photos, but told me they weren’t into girls and didn’t want to join a couple. She did say that she was interested in meeting up just with me though. Read more »